CN103755594A - Preparation method for tetrachloro-o-nitrile methyl benzoate - Google Patents
Preparation method for tetrachloro-o-nitrile methyl benzoate Download PDFInfo
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- CN103755594A CN103755594A CN201310738456.3A CN201310738456A CN103755594A CN 103755594 A CN103755594 A CN 103755594A CN 201310738456 A CN201310738456 A CN 201310738456A CN 103755594 A CN103755594 A CN 103755594A
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- tetrachloro
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- itrile group
- methyl benzoate
- benzoate
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Abstract
The invention discloses a preparation method for tetrachloro-o-nitrile methyl benzoate. The preparation method for tetrachloro-o-nitrile methyl benzoate comprises the following steps: mixing tetrachloro-o-nitrile ammonium benzoate, a phase transfer catalyst and ester organic solvents, adding a methylation reagent and stirring to react, and after the reaction is concluded, collecting a target product, namely tetrachloro-o-nitrile methyl benzoate, from the reaction products. According to the preparation method for tetrachloro-o-nitrile methyl benzoate disclosed by the invention, the phase transfer catalyst is used, low-toxicity ester solvents can be selected to react, the reaction is performed at a low temperature, the dosage of virulent dimethyl sulphate is low, the by-products are few, the reaction time is short, and the yield is high; defects existing in the prior art are overcome; the preparation method is a production method for tetrachloro-o-nitrile methyl benzoate, which is moderate in reaction conditions, environment-friendly, short in reaction time, and high in yield.
Description
Technical field
The present invention relates to the synthesis technique of the adjacent itrile group methyl benzoate of tetrachloro.
Background technology
The adjacent itrile group methyl benzoate of tetrachloro is the intermediate for the preparation of a kind of pigment dyestuff, prior art is take butanone, methyl alcohol and toluene etc. as solvent, under reflux temperature, react, the shortcoming of its technique is, the methyl-sulfate usage quantity of severe toxicity is larger, and temperature of reaction is high, and energy consumption is large, by product is many, and the solvent of use is poisoned large to environment and human body.
Summary of the invention
The object of the present invention is to provide the preparation method of the adjacent itrile group methyl benzoate of a kind of tetrachloro,
Method of the present invention, comprises the steps:
After adjacent tetrachloro itrile group ammonium benzoate, phase-transfer catalyst and ester class organic solvent are mixed, add methylating reagent methyl-sulfate stirring reaction, temperature of reaction is 20 ℃ ~ 60 ℃;
In said process, the reaction times is 2 ~ 3h, and preferably 2.5h after reaction finishes, collects target product from reaction product, the adjacent itrile group methyl benzoate of tetrachloro;
The method of described collection target product, comprises filtration successively, washing, and water layer is separation with organic layer, and organic layer underpressure distillation organic solvent obtains the adjacent itrile group methyl benzoate of tetrachloro.
Described esters solvent is selected from ritalin, vinyl acetic monomer, N-BUTYL ACETATE or methylcarbonate;
Described phase-transfer catalyst is selected from Tetrabutyl amonium bromide, tetrabutylammonium chloride, hexaoxacyclooctadecane-6 or benzyltriethylammoinium chloride, and preferably tetrabutylammonium chloride is catalyzer;
The weight proportion of the adjacent itrile group ammonium benzoate of methyl-sulfate and tetrachloro is between 0.5: 1 ~ 0.42: 1, and best proportioning is 0.438: 1;
The weight proportion of the adjacent itrile group ammonium benzoate of phase-transfer catalyst and tetrachloro is 0.03: 1 ~ 0.15: 1; Best proportioning is 0.1: 1.
The weight proportion of the adjacent itrile group ammonium benzoate of esters solvent and tetrachloro is 2.5: 1 ~ 3: 1;
Advantage of the present invention is, adopts phase-transfer catalyst, can select the esters solvent of low toxicity to react, and reaction is carried out at lower temperature, and the consumption of the methyl-sulfate of severe toxicity is few, and by product is few, and the reaction times is short, and yield is high.The defect existing to overcome prior art.For the production method of a kind of reaction conditions gentleness, the adjacent itrile group methyl benzoate of the tetrachloro that environmentally friendly, the reaction times is short, yield is high.
Embodiment
Embodiment 1
In reactor, drop into the adjacent itrile group ammonium benzoate of 1000Kg tetrachloro, 10Kg catalyzer tetrabutylammonium chloride, 4000Kg methylcarbonate, after stirring, continue to add 438Kg methyl-sulfate, continue to stir, insulation reaction 2.5h at 30 ℃, to said mixture pressure filter press filtration, collects filtrated stock, add 500Kg water, layering after stirring, collected organic layer, underpressure distillation obtains the adjacent itrile group methyl benzoate of 940.5Kg tetrachloro after going out organic solvent.
Embodiment 2
In reactor, drop into the adjacent itrile group ammonium benzoate of 1000Kg tetrachloro, 10Kg catalyzer Tetrabutyl amonium bromide, 4000Kg vinyl acetic monomer, after stirring, continue to add 438Kg methyl-sulfate, continue to stir, insulation reaction 2.5h at 30 ℃, to said mixture pressure filter press filtration, collects filtrated stock, add 500Kg water, layering after stirring, collected organic layer, underpressure distillation obtains the adjacent itrile group methyl benzoate of 953Kg tetrachloro after going out organic solvent.
Claims (6)
1. the preparation method of the adjacent itrile group methyl benzoate of tetrachloro, it is characterized in that, after comprising the steps: adjacent tetrachloro itrile group ammonium benzoate, phase-transfer catalyst and ester class organic solvent to mix, add methylating reagent stirring reaction, after reaction finishes, from reaction product, collect target product, the adjacent itrile group methyl benzoate of tetrachloro.
2. method according to claim 1, is characterized in that, methylating reagent is methyl-sulfate.
3. method according to claim 1, is characterized in that, temperature of reaction is 20 ℃ ~ 60 ℃; Reaction times is 2 ~ 3h.
4. method according to claim 1, is characterized in that, the method for described collection target product, comprises filtration successively, washing, and water layer is separation with organic layer, and organic layer underpressure distillation organic solvent obtains the adjacent itrile group methyl benzoate of tetrachloro.
5. according to the method described in claim 1 ~ 4 any one, it is characterized in that, described esters solvent is selected from ritalin, vinyl acetic monomer, N-BUTYL ACETATE or methylcarbonate; Described phase-transfer catalyst is selected from Tetrabutyl amonium bromide, tetrabutylammonium chloride, hexaoxacyclooctadecane-6 or benzyltriethylammoinium chloride.
6. method according to claim 5, is characterized in that, the weight proportion of the adjacent itrile group ammonium benzoate of methyl-sulfate and tetrachloro is 0.5: 1 ~ 0.42: 1; The weight proportion of the adjacent itrile group ammonium benzoate of phase-transfer catalyst and tetrachloro is 0.03: 1 ~ 0.15: 1; The weight proportion of the adjacent itrile group ammonium benzoate of esters solvent and tetrachloro is 2.5: 1 ~ 3: 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201310738456.3A CN103755594A (en) | 2013-12-30 | 2013-12-30 | Preparation method for tetrachloro-o-nitrile methyl benzoate |
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| CN201310738456.3A CN103755594A (en) | 2013-12-30 | 2013-12-30 | Preparation method for tetrachloro-o-nitrile methyl benzoate |
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| CN103755594A true CN103755594A (en) | 2014-04-30 |
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| CN201310738456.3A Pending CN103755594A (en) | 2013-12-30 | 2013-12-30 | Preparation method for tetrachloro-o-nitrile methyl benzoate |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110818591A (en) * | 2019-11-15 | 2020-02-21 | 彩客化学(沧州)有限公司 | Preparation method of methyl 3,4,5, 6-tetrachloro-2-cyanobenzoate |
Citations (7)
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|---|---|---|---|---|
| US2964533A (en) * | 1957-12-19 | 1960-12-13 | Geigy Ag J R | Heterocyclic compounds and process for the production thereof |
| DE1113276B (en) * | 1957-12-17 | 1961-08-31 | Geigy Ag J R | Process for the production of colored condensation products |
| US3979386A (en) * | 1973-05-29 | 1976-09-07 | Ciba-Geigy Corporation | Iminoisoindoline pigments and processes for the preparation thereof |
| EP0097615A1 (en) * | 1982-06-17 | 1984-01-04 | Ciba-Geigy Ag | Preparation of cyanobenzoic-acid esters |
| US4978768A (en) * | 1986-01-15 | 1990-12-18 | Ciba-Geigy Corporation | Process for the preparation of alkyl esters of tetrachloro-2-cyano-benzoic acid |
| JP2004307854A (en) * | 2003-03-27 | 2004-11-04 | Toyo Ink Mfg Co Ltd | Transparent coloring composition and color filter |
| WO2008096371A1 (en) * | 2007-02-05 | 2008-08-14 | Sudarshan Chemical Industries Ltd. | Isoindolinone pigments and a method of manufacturing. |
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2013
- 2013-12-30 CN CN201310738456.3A patent/CN103755594A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1113276B (en) * | 1957-12-17 | 1961-08-31 | Geigy Ag J R | Process for the production of colored condensation products |
| US2964533A (en) * | 1957-12-19 | 1960-12-13 | Geigy Ag J R | Heterocyclic compounds and process for the production thereof |
| US3979386A (en) * | 1973-05-29 | 1976-09-07 | Ciba-Geigy Corporation | Iminoisoindoline pigments and processes for the preparation thereof |
| EP0097615A1 (en) * | 1982-06-17 | 1984-01-04 | Ciba-Geigy Ag | Preparation of cyanobenzoic-acid esters |
| US4978768A (en) * | 1986-01-15 | 1990-12-18 | Ciba-Geigy Corporation | Process for the preparation of alkyl esters of tetrachloro-2-cyano-benzoic acid |
| JP2004307854A (en) * | 2003-03-27 | 2004-11-04 | Toyo Ink Mfg Co Ltd | Transparent coloring composition and color filter |
| WO2008096371A1 (en) * | 2007-02-05 | 2008-08-14 | Sudarshan Chemical Industries Ltd. | Isoindolinone pigments and a method of manufacturing. |
Non-Patent Citations (2)
| Title |
|---|
| PUGIN, A. ETAL: "Organic pigments: derivatives of 4,5,6,7-tetrachloroisoindolin1-one, their", 《 CONGR.》, vol. 7, 31 December 1964 (1964-12-31), pages 61 - 73 * |
| 韩巧凤等: "《催化材料导论》", 31 March 2013, article "相转移催化剂", pages: 38 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110818591A (en) * | 2019-11-15 | 2020-02-21 | 彩客化学(沧州)有限公司 | Preparation method of methyl 3,4,5, 6-tetrachloro-2-cyanobenzoate |
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Inventor after: Shen Xing Inventor after: Li Xiujuan Inventor after: Mao Bengang Inventor before: Shen Xing |
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Application publication date: 20140430 |
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